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Sen. Robert Menendez’s potentially problematic ties to friend and political donor Salomon Melgen came under further scrutiny late Thursday with a New York Times report detailing the mutually financially beneficial tenor of a decadeslong relationship between the New Jersey Democrat and the Florida eye doctor.

Federal agents raided Melgen’s medical practice in West Palm Beach earlier this week in what news reports linked to an alleged travel and prostitution scandal.

The Times report focuses on Melgen’s purchase two years ago of an ownership stake in the Caribbean port-security company ICSSI and Menendez’s subsequent use of his congressional subcommittee chairmanship to push U.S. government officials to intervene and enforce a contract worth as much as $500 million.

Menendez, meanwhile, benefitted from campaign fundraisers thrown by Melgen’s wife at their Dominican Republic estate. Melgen’s company also donated $700,000 in the months leading up to the November elections to a super PAC that dumped $582,500 into Menendez’s re-election bid.

Menendez has acknowledged he took several flights on Melgen’s private plane to the Dominican Republic that were not initially disclosed as gifts on his financial disclosure forms and said he has since repaid Melgen’s company $58,500 for the flights.

Aides to Menendez, who is set to assume the chairmanship of the full Senate Foreign Relations Committee, confirmed to the Times that the senator spoke to State Department officials about the contract. Menendez also raised the issue during a Senate Foreign Relations Subcommittee on the Western Hemisphere hearing last summer.

Menendez Chief of Staff Daniel O’Brien told the Times that the senator has always stood up for “U.S. companies that are not being treated fairly or have issues pending in foreign countries.”

The Senate Ethics Committee does not comment on pending cases and will not confirm whether it has opened any sort of formal probe of Menendez’s dealings. Ranking Member Johnny Isakson, R-Ga., told the Washington Post the panel was “aware” of the media reports.

Public corruption statutes prohibit public officials from engaging in so-called quid pro quo schemes, which are considered a form of bribery, but it is an amorphous standard that is difficult to prosecute. Evidence of a long-term friendship or personal relationship would only complicate such a case.

An overview of the Senate’s code of conduct and ethics rules prepared by the Senate Ethics Committee during the 112th Congress states that lawmakers “may not receive compensation from any source because of improper influence exerted from their position as a Member, officer, or employee of the Senate.” They likewise may not “solicit or receive compensation for representing another person or entity before a government agency in a manner in which the U.S. government has an interest.”

It is unclear what if any laws or rules may apply to the Menendez’s dealings with Melgen.